5-(二甲氨基)戊-3-炔-1-醇 | 104602-35-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 5-(二甲氨基)戊-3-炔-1-醇
• 英文名称: 5-dimethylamino-pent-3-yn-1-ol
• 英文别名: 1-Dimethylamino-5-hydroxy-pent-2-in；1-Dimethylamino-pentin-(2)-ol-(5)；1-dimethylamino-2-pentyn-5-ol；5-Dimethylamino-pent-3-in-1-ol；5-(Dimethylamino)pent-3-YN-1-OL
• CAS: 104602-35-9
• 化学式: C₇H₁₃NO
• 分子量: 127.186
• InChiKey: BWIBQBNCUFUKEX-UHFFFAOYSA-N

物化性质

• 沸点：
  77 °C(Press: 0.05 Torr)
• 密度：
  0.962±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(二甲氨基)戊-3-炔-1-醇 在 氨 、 sodium amide 作用下， 生成 (5-methoxy-pent-2-ynyl)-dimethyl-amine
  参考文献：
  名称：

  Guermont, Bulletin de la Societe Chimique de France, 1953, p. 386,389

  摘要：

  DOI：
• 作为产物：
  描述：

  Dimethyl-<3-chlor-but-2-en-1-yl>-<5-hydroxy-3-chlor-pent-2-en-1-yl>ammonium chlorid 在 hydroxide 作用下， 生成 5-(二甲氨基)戊-3-炔-1-醇
  参考文献：
  名称：

  Babayan,A.T. et al., Journal of general chemistry of the USSR, 1963, vol. 33, p. 2127 - 2129

  摘要：

  DOI：

文献信息

• A Superior Non-Symmetrical NCP Pincer Type Palladacycle Catalyst Precursor for the Coupling of Aryl Boronic Acids with Aryl Chlorides
  作者：Jairton Dupont、Adriano L. Monteiro、Gilber R. Rosa、Gunter Ebeling

  DOI：10.1055/s-2003-44352

  日期：——

  The air and water stable non-symmetrical pincer palladacycle [Me2NCH2(Cl)C=C(CH2)2OP(i-Pr)2-kNkCkP]PdCl 5, easily prepared from the chloropalladation of the hetero-substituted alkyne Me2NCH2C≡C(CH2)2OP(i-Pr)2, is a highly efficient catalyst precursor for the coupling of aryl boronic acids and aryl chlorides. Both electron-rich and electron-poor aryl chlorides are efficiently coupled in the presence of 5 to furnish the corresponding cross-coupled products in excellent yields, and a wide variety of functional groups are tolerated in both aryl chloride and aryl boronic acid.

  由杂取代炔 Me2NCH2C≡C(CH2)2OP(i-Pr)2 的氯钯化反应简易制备而成的空气和水稳定的非对称钳形链锁[Me2NCH2(Cl)C=C(CH2)2OP(i-Pr)2-kNkCkP]PdCl 5 是芳基硼酸和芳基氯化物偶联反应的高效催化剂前体。在 5 的存在下，富电子和贫电子的芳基氯化物都能高效地偶联，以优异的产率得到相应的交叉偶联产物，而且芳基氯化物和芳基硼酸中都能容许多种官能团。
• Aminomethylation of acetylene alcohols and their esters with gem-diamines catalyzed by complexes of d-transition and rare-earth metals
  作者：M. G. Shaibakova、I. G. Titova、A. G. Ibragimov、U. M. Dzhemilev

  DOI：10.1134/s1070428011020023

  日期：2011.2

  An efficient synthetic procedure was developed for preparation of oxygen-containing propargylamines with high yields and selectivity by aminomethylation of propargyl alcohols and their esters with gem-diamines catalyzed by complexes and salts of d-transition metals and lanthanides.
• The retro-chloropalladation reaction of heterosubstituted alkynes
  作者：Mara L. Zanini、Mario R. Meneghetti、Gunter Ebeling、Paolo R. Livotto、Frank Rominger、Jairton Dupont

  DOI：10.1016/s0277-5387(03)00324-3

  日期：2003.7

  The bridge-splitting reaction of dimeric palladacycles of the type Pd[kappa(1)-C, kappa(1)-N-C(R) = C(Cl)CH2NMe2](mu-Cl)}(2) (R = Ph, Me, CH2CH2OH), derived from the chloropalladation of propargyl amines (RCdropCCH(2)NMe(2)), with pyridine (Py), triphenylphosphine (PPh3) and tert-butytisonitrile ((BuNC)-Bu-t) affords the monomeric compounds [PdC(R)=CCH2NMe2(Cl)L] (L = Py, PPh3, (BuNC)-Bu-t). These monomeric compounds are not stable in solution and undergo retro-chloropalladation reactions yielding the propargyl amines and [PdCl(L)-mu-Cl](2). This process is strongly dependent upon the nature of the incoming nucleophile (L), the R group on the metallated ligand and the temperature. The retro-halopalladation reaction is almost instantaneous in the case of the reaction of the bromo derivative [PdC(Ph)=C(Br)CH2NMe2-mu-Br](2) and pyridine at room temperature. These results can be rationalized in terms of the stability of the Pd-C bond of the intermediate monomeric compound [PdC(R)=C(X)CH2NMe2(X)L], that is directly related to the nature of its substituents R (Ph, Me and CH2CH2OH), of ligands which are both cis and trans to it (Py, (CNBu)-Bu-t, PPh3, Cl and Br) and the temperature. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Olomucki, Annales de Chimie (Cachan, France), 1960, vol. <13> 5, p. 845,871
  作者：Olomucki

  DOI：——

  日期：——
• Marszak et al., Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1950, vol. 231, p. 1578
  作者：Marszak et al.

  DOI：——

  日期：——